high-throughput determination of log D values by lc/ms method in .NET

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high-throughput determination of log D values by lc/ms method
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THRX-126276 2
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1.5 log D THRX-164446 1 THRX-913770 0.5 THRX-145495 0 0 -0.5 1 2 3 4 Mixing Method 5 6
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THRX-126276 THRX-164446 THRX-913770 THRX-145495
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Figure 17.4. Log D values obtained from four mixing methods. 0 = tubes; 1 = end-over-end 1 h; 2 = end-over-end 4 h; 3 = horizontal shaker 1 h; 4 = vertical shaker 1 h.
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1 A B
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Left side (C1-F1), 0.15 0.023
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Upper left corner (A1-A4), -0.03 0.018
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Upper right corner (A9 - A12), -0.06 0.013
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Figure 17.5. Evaluation of edge effect using Scopolamine as the model compound.
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Edge Effect Experiment Since a 96-well plate is a two-dimensional device, an experiment was designed to ensure the reliability of the results from wells at different positions. This experiment tested the edge-to-edge effect of the 96-well plate when using the Apricot pipettor for solvent addition and dilution. The compound used for this experiment was scopolamine, and the plate was set up as shown in Figure 17.5. Log D values of scopolamine obtained from dif-
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results and discussion
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ferent locations of the plate are summarized in Figure 17.5. The log D values were consistent throughout the plate, except those obtained from the upper left corner and the upper right corner, which were slightly lower than the rest. However, the absolute difference between any two groups was less than 0.23, which is within the acceptable accuracy range of the current method. 17.3.2. LC/MS Method Development
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An LC/MS method, in general, has a signi cantly higher signal-to-noise ratio than that of a LC/UV method. More important, MS offers unique speci city that no other technique can. For example, Figure 17.1 shows the comparison of the LC/MS and LC/UV data. It is very dif cult to pinpoint exactly which peak is the peak for the compound of interest. Based on peak height, the peak at 3.72 minutes would be selected in frame B. However, MS data indicate that the peak at 3.72 minutes does not have the right mass. If we take retention time as a guide that eliminates the peaks at 3.72 and 3.82 minutes, three possibilities exists: 2.55, 2.65, and 2.74 minutes. If the right peak were chosen, the small size of the peak would make it dif cult to provide accurate quantitative information. On the other hand, LC/MS can easily identify which peak is correct. We can see from Figure 17.1A that when selective ion monitoring (SIM) is used for detection, only one peak with the correct mass can be detected. The signi cantly higher signal-to-noise ratio of the MS data makes the quantitation of the LC/MS method very reliable. However, LC/MS, though speci c, may not always be accurate in automatically determining the exact amount of compound present. Other factors have to be considered as well. For example, in these experiments LC/MS combined with electrospray ionization (ESI) generated a nonlinear response curve. As the concentrations in the two phases, octanol and aqueous, are often different, this nonlinearity makes it dif cult to determine the log D values by simply comparing the ratios of the peak areas of the compound in two phases. Fortunately, when atmospheric pressure chemical ionization (APCI) instead of ESI is used as the ionization method, a reasonably large range of concentrations give linear responses for all of the compounds tested. Thus APCI appears to be better than ESI as an ionization method for quantitation purposes. APCI is generally regarded as being more robust and less susceptible to ion suppression than electrospray ionization.18 19 It was found that at least two orders of magnitude for linearity can be easily obtained by the LC/APCI-MS method. For example, Figure 17.6A shows that the response of lidocaine is linear (R2 0.999) within the concentration ranges of 0.1 to 12.5 mM (125-fold). Figure 17.6B shows that the response of three
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